Older Lesbian Stories
![](/file/9d11000d16f29988389bc.gif)
🔞 ALL INFORMATION CLICK HERE 👈🏻👈🏻👈🏻
Older Lesbian Stories
If playback doesn't begin shortly, try restarting your device.
Videos you watch may be added to the TV's watch history and influence TV recommendations. To avoid this, cancel and sign in to YouTube on your computer.
An error occurred while retrieving sharing information. Please try again later.
0:02 / 13:15 • Watch full video Live
I wanted to see myself as the cool, hip queer I hoped I was: someone who doesn’t have to subscribe to retrograde and patriarchal notions of what love is, or could be.
“My friends and I don’t wanna be here if this isn’t an actively trans-affirming space. I’m only coming if all my sisters can.”
Our identity hasn’t been able to shake the anti-gay stereotypes of lesbians as uncosmopolitan boomer TERFs, sporting Tevas and cargo pants covered in cat hair.
“I don’t have a husband,” I said. “I’m gay. We’re all gay.”
Olivia is one of the last dedicated venues for lesbian debauchery still standing.
From the very beginning, we moved as if we’d known each other a long, long time.
I saw how much pride she took in her butch womanhood, which wasn’t some androgynous nowhere zone — femininity’s absence — but a whole universe unto itself.
We did a lap around the upper deck before sunset, arms linked, and when we arrived back on the main deck, a big group of lesbians literally cheered .
She told me she’d lived on this earth for 53 years. She knew what she wanted. And now it was my turn to figure that out for myself.
Your weekday morning guide to breaking news, cultural analysis, and everything in between
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
I didn’t expect that spending a week with a couple thousand lesbians on a cruise ship would push me to radically reconsider the future I’d planned for myself.
It’s night four of the cruise — karaoke night — and everybody’s been picking slow, sad songs. So I decide to wake the place up a little.
The second dinner session has just let out, and the Rendezvous Lounge (which is as tacky as it sounds) is overflowing with lesbians. They’re mostly middle-aged or older; they’re wearing brightly colored tourist T-shirts purchased on our excursion earlier today to St. Kitts; they’re cheering for their new friends; they’re here to have a good time.
I’m determined to do something showstopping, but our offerings are comically limited. No Sheryl Crow, no Michelle Branch. Not even “Total Eclipse of the Heart.”
“These choices are homophobic,” I tell my new friend Dana. She’s technically my press handler, tasked with making sure I see the best that the tour operator, Olivia Travel, has to offer. So far, she’s more than delivered, but the weak karaoke selection — not Dana’s fault! — is a rare low point on a trip that, four days in, has already slowly but surely begun to change my life.
I settle for some Kelly Clarkson, and after my screechy but enthusiastic rendition of “Since U Been Gone,” five (!) different women approach me, complimenting my performance. One of them tells me her friend thinks I’m really cute, and could she buy me a drink?
I’m loose and light and a little sleepy from my second Corona and a blossoming sunburn. Sure, I say, why not, thinking all the while: If any other 27-year-old lesbians could use a self-esteem boost, all they need to do, clearly, is get themselves on an Olivia cruise.
I had only a vague idea of what to expect when I boarded the Celebrity Summit in April for a weeklong excursion to the Caribbean. Olivia, a groundbreaking women’s record label turned lesbian travel company, named for the hero of a Dorothy Bussy novel, has catered specifically to lesbian vacationers since its maiden voyage in 1990. When I reached out to Olivia, the company offered me a press ticket for one of its Celebrity-partnered cruises so that I could get a sense of how it's become one of the most successful lesbian companies of all time . I generally expected to meet some nice older ladies with interesting life stories, to explore the tensions of intergenerational lesbian culture and the fraught future of lesbian spaces, to laze about on a beach in the Virgin Islands and get to say I was swimming and sunbathing “for work.”
What I didn’t expect was everything else that would happen to me — and is still happening to me — thanks to this one little week in my otherwise pleasantly uneventful life.
For one thing, I didn’t expect to have nearly so much fun. I’d been on one cruise before, also to the Caribbean, but I was too little at the time to really remember it. And were it not for this story, there’s no way I would have voluntarily set foot on a cruise ship again. Even though cruise companies are actively trying to capture the millennial dollar , which is sort of working , cruises still aren’t exactly a popular travel option for my peer group; we tend to favor more “ authentic ” travel experiences (whatever that means). And we have plenty of reasons to avoid cruises: Operators exploit their workers ; passengers experience alarmingly high rates of sexual assault ; and the ships destroy the environment , disrupt local communities , and generally disgorge terrifying crowds of oblivious and often racist white people into historic ports, where they can cause a few hours’ worth of chaos before sailing off to their next destination. It’s a particularly ugly (and expensive ) brand of tourism.
So I’m surprised to say I might actually travel with Olivia again, skeptical as I remain of cruise ethics in general. And that’s because of all the things that happened in the eight days I spent aboard the Summit — things I wasn’t remotely expecting.
I didn’t expect to have a profound reckoning with my relationship to my own lesbianism and womanhood. I didn’t expect to make friends I hope to keep for a long, long time. I didn’t expect that spending a few days with a couple thousand lesbians on a floating hotel/casino/mall/amusement park would push me to radically reconsider the future I’d been carefully and painstakingly planning for myself.
Most of all, I didn’t expect to meet Lynette.
When I boarded the cruise at the end of April, my partner of nearly five years and I had been experimenting with nonmonogamy. When we met, we’d been two postgrad dirtbags, drinking beer out of paper bags in the park on weekday afternoons, sleeping on air mattresses and in hallways. I had a full-time media fellowship that paid me $20,000 a year; they were a bike courier, delivering food to rich people’s apartments, and working the late shift at REI, stocking while I slept. We’d see each other early in the mornings; they’d bring me donuts in bed.
Then somehow, all of a sudden, years passed. We became two professionals in our late twenties, living in our dream apartment on the top floor of a Brooklyn brownstone. We weren’t allowed to have pets, but, like good millennials, we had plenty of plants, and interests outside of each other: my roller derby, their ultramarathons. We were busy, stable. Happy enough.
I tried to tell myself that lesbian bed death isn’t real , all the while heartily blaming myself for our increasingly diminished sex life. I was the one who never really felt like initiating, or at least not with anywhere near the regularity we’d had as a hormone-crazed new couple. I assumed, at best, that all passions cool somewhat over the years; at worst, I thought something might be wrong with me.
My partner was patient and kind. But as time went on, they got frustrated — understandably — and they suggested, as a reparative measure, that we open up our relationship.
I was hesitant for a couple reasons. The first was that they’d slept with someone else, just once, when they were on a solo vacation, before we’d agreed to any sort of open-relationship terms; I felt like they’d forced my hand. (It’s hard for me even now to say they cheated on me, though that’s precisely what they did.) The second reason was that I’d watched some of my friends in long-term relationships experiment with nonmonogamy, only for the experiment to end in disaster: Somebody, inevitably, fell for somebody else.
In the end, I decided to give it a shot. I was starting to get nervous, nearly five years in, about what our future had in store for us. I’m a long-term kind of planner, while my partner was more likely to fly by the seat of their pants. I wanted kids; they were less sure. I wanted to spend our shared time and money on building a true home together; they were happy to live indefinitely out of milk crates. I wanted to stay in New York; they were feeling pulled back toward the Mountain West, where they’d grown up.
Nonmonogamy, then, seemed like a sort of part-time solution to much deeper issues I wasn’t yet ready to grapple with. So I decided to believe in the potential of openness to enrich a relationship, rather than to unravel it.
Before I went on the cruise, not much had actually happened in the nonmonogamy department. Once, after a friend’s party in Brooklyn, I drunkenly took a cab into Manhattan alone and picked up a girl at the borough’s only good lesbian bar, Cubbyhole. It was a perfectly nice experience, but when I got home and spent the day on my couch, sick from binge-drinking my way into someone else’s bed, I tried to figure out how to feel. Later, when my partner started sleeping with a friend of a friend, I was no more equipped to sort through my mess of emotions (sadness, ambivalence, relief).
Nonmonogamy is hardly scandalous or even really notable these days. In some of my queer circles, in fact, monogamy is the rarer beast. There’s nothing inherently more ~radical~ about either lifestyle. Still, in opening up my relationship — and in trying to convince myself that maybe I didn’t want marriage or kids or the trappings of conventional adulthood — I wanted to see myself as the cool, hip queer I hoped I was: someone who doesn’t have to subscribe to retrograde and patriarchal notions of what love is, or could be.
The night before I left on the cruise, two of my best friends got married. Watching one of my friend’s dads talking at the wedding dinner about how much he loved his daughter and her new wife, I teared up a little and said something to my partner about it: “This is actually pretty nice, huh?” But they wrinkled their nose at me. They’re not a fan of weddings — the pomp and circumstance, the big, grand displays of public affection.
I know this. And I get it. But this particular wedding, for friends we love, wasn’t something ostentatious and flashy; it was a tiny ceremony at city hall, a simple dinner, drinks at a bar afterward in Brooklyn. Was that so bad, really, to want?
My first day on the cruise, Saturday, I was hungover and exhausted. I’d been up late celebrating at the wedding, slept through my alarm, and barely made my flight to Puerto Rico. After deplaning and bumbling my way through the cruise check-in, I crashed in my quarters for a two-hour hangover nap. When I woke to the gorgeous sight of water and sun outside my personal patio, I felt a little sad and a little lonely. I wished I could have scooped up the entire wedding party and taken them with me to San Juan.
This was Dana’s first Olivia cruise too, though she’d been working for a while as the company’s content strategist. The staff thought that since she and I had similar backgrounds, it would make sense for Dana to take me under her wing this trip. She’s a pink-haired ball of zany energy who, from the moment I showed up on the dock in San Juan, made me feel like I was where I belonged. And we had plenty to talk about, since she’s an LGBT media person too — the managing editor of Bella Media , a ClexaCon moderator , lesbian romance author , and a veteran editor and writer of the site AfterEllen, from back when it used to be good (nowadays it’s an anti-trans pile of garbage ).
When we boarded, Dana introduced me to the adorable boomer-millennial pair in charge of Olivia’s Solos Program, which caters to women (single or partnered) who decide to go on trips alone. I got my own Solos dog tag and a pink Olivia bracelet to signify my newbie status.
Even though the Solos Program meant that at every meal there’d be a designated Solos table where I could sit with other single travelers, I was still a little intimidated by the prospect of finding people to hang out with all week. So I felt grateful to Dana, who accompanied me to my first Solos dinner that night. Later that week, we’d have a couple long dinners, just the two of us, indulging in the obscene number of courses you’re afforded during a cruise meal and bonding over the strange particularities of being a professional homosexual. I knew I was supposed to be becoming pals with fellow cruisers, not the staffer who was basically being paid to be my friend. But I figured I still had time.
When I first pitched this story to my editors, I thought I’d be reporting on a lesbian cultural artifact in its twilight years. The women who’ve faithfully gone on dozens of Olivia trips over the decades are getting older, and I didn’t have a lot of faith that younger queer people were going to step in and save companies like this from extinction. Other elements of lesbian culture have been steadily dying ; why should Olivia be any different?
The first time I thought that Olivia might actually stand a chance at survival was Sunday, the first full day of the cruise, when I attended the welcome mixer for “Generation O,” which is how Olivia refers to its precious few millennial and Generation X clientele. As I walked around the ship, which holds over 2,000 passengers, it was already clear that the average woman here was a couple decades older than me. But it turned out that there were a few other twenty- and thirtysomethings who’d managed to find their way to Olivia.
Dana was at the mixer, as well as another staffer, Ingrid, a cheery femme redhead and Olivia’s program manager. The three of us were, for the first few minutes, the only people in the room — we’d commandeered the nightclub during daylight hours — but slowly, a crowd of around 20 other people trickled in. According to everyone’s awkward intros, they were from all over the country: Denver, San Diego, Seattle, Nashville, Houston, New York.
We all formed one big circle, and the staffers got the ball rolling. First things first: How had we all heard about Olivia?
Someone mentioned getting a brochure in the mail after they’d given Olivia their contact info years ago (“You guys must be running the lesbian mafia”). Others had come to see LP, one of the lesbian musicians headlining this trip, or because — like me — they’d seen the iconic L Word episode that takes place aboard an Olivia cruise.
One woman, my soon-to-be-friend Jamie (not her real name; she asked that I withhold her identity due to the sensitive nature of her work), told the group that she’d taken her first cruise with a partner, hoping to “slow down and be bored.” That plan turned out to be “a total disaster” — they had a blast. Now Jamie was back for her second Olivia cruise with her partner Matie, who runs Self Serve , a sexuality resource center and sex shop in Albuquerque, New Mexico; their other partner was stuck at home, studying for exams.
A 36-year-old hairdresser said she’d won Olivia tickets at a pride event and had no idea what to expect. Then, on the cruise, she met a bunch of older women who “have had a harder time than we could dream of, and yet they’re so free. It became this…spiritual experience, almost. To see all these older pairs of hands holding each other — it was so beautiful and safe.”
After everyone had doled out sufficient praise for the company, the conversation quickly turned, in perhaps inevitable millennial fashion, to everything Olivia could be doing a better job of when it comes to attracting a younger generation of queers.
Some people suggested that Olivia offer scholarships or student discounts, since cruising is so expensive. If Olivia hadn’t comped my ticket, my room on Deck 8, with its own private veranda, would have cost me either $2,599 or $3,399, depending on how early I’d booked. That price covered my room and all my food on board, but alcohol and any “special” beverages would cost me a few hundred extra. The cheapest room on this trip, an interior stateroom with no veranda or window, would have been $999 per person as an early bird special or $1,299 at regular price. That’s more reasonable, especially with a payment plan, but Olivia’s best deals tend to sell out extremely quickly, sometimes a year or two in advance. And Olivia’s resort offerings, which skew younger, aren’t much cheaper than the cruises — sometimes they’re even more expensive . Now that international travel has become more affordable than ever, it’s hard to convince a young person that Olivia’s hefty price tag is worth it.
Someone mentioned that they were surprised there were no sex toys available for sale on board. Another mentioned loving A-Camp , a planned getaway offered by the queer women’s website Autostraddle, for all the fresh activities it offered. Women from smaller cities thought Olivia could do a better job marketing outside of New York, San Francisco, and LA: “A lot of gay people don’t live in those places.”
But the main question concerning Olivia’s younger guests, which we’d spend the rest of the mixer discussing at length: How welcoming was Olivia to trans travelers, particularly trans women?
Jamie mentioned that she’d previously passed on an Olivia cruise when she saw that a speaker booked for the trip was Lisa Vogel. Vogel, the creator and producer of the Michigan Womyn’s Music Festival, shut down the lesbian feminist women’s gathering in 2015 — closing its doors entirely, after 40 years as a safe haven of living lesbian history, rather than allowing out trans women to attend. For a lot of millennial queer women, myself included, MichFest is the perfect example of something beautiful and sacred we would have loved to take part in — something we’d be forever thankful for — if only, if only , they hadn’t seen trans women as the enemy.
When booking her cruise this time around, Jamie said she was frustrated that Olivia’s website didn’t explicitly make clear that the trips welcome trans women; she had to call the offices to double-check. “My friends and I don’t wanna be here if this isn’t an actively trans-affirming space. I’m only coming if all my sisters can.” (At karaoke later in the week, a young trans guy who’d been at the meetup would introduce himself to Jamie and thank her for speaking up.)
Later in the week, Tisha Floratos, the vice president of travel for Olivia, told me that she and her staff think about this a lot. “We’ve talked about how we begin to promote inclusivity while also preserving our core: that this is a company for lesbians. We don’t publicly, historically, say that we’re trans inclusive, but we’re always welcoming to our trans guests.”
At the Gen O meetup, the hairdresser mentioned that most of the paying customers on board are older women who’ve had an extraordinarily difficult time navigating life as lesbians; they deserve a space, she said, to fully be themselves. Maybe Olivia could do a specific queer-plus trip for trans people and gay men? Being in a space with “someone who looks like a man,” she said — horrifying me, Jamie, Matie, Dana, and a bunch of others — “can cause these women so much trauma.”
The room exploded. Eventually, after a few minutes of impassioned back-and-forth, the group’s conversation wrapped up more or less amicably. But I left the meetup keenly aware of how much there was for all of the cruise’s passengers — despite what we had in common — to disagree about.
Original Olivia Records Collective: Judy Dlugasz, Meg Christian, Ginny Berson, Jennifer Woodul, and Kate
Dirk Caber
Bigboobs Hardcore
Short Erotic Sex Stories